The billionaire executive has been applauded for his inspirational pursuits with charity, but his bizarre opinions have shocked and confused many over the years.
Earlier this year he walked back on comments suggesting gruelling 12-hour work days common in China's tech and internet industries were a "blessing".
Ma came out in support at the time of the so-called "996-system" — 9am to 9pm, six days a week — saying it had helped tech giants like Alibaba, JD.com and Tencent experience unprecedented growth.
Disgruntled software developers formed a discussion group on the codesharing platform Github called "996. ICU", suggesting working 996 could send workers to the intensive care unit.
"I personally think that being able to do 996 is a huge blessing that many companies and employees do not have the opportunity to have," Ma said at an internal company event, a transcript of which was published on Alibaba's WeChat account.
"If you do not do 996 when you are young, when will you? Do you think never having to work 996 in your life is an honour to boast about? If you join Alibaba, you should get ready to work 12 hours a day, otherwise why do you come to Alibaba? We do not need those who comfortably work eight hours."
He added, "If you do not pay the price, how will you gain?"
However, Ma eventually clarified his controversial opinion, explaining that working such long hours permanently was "unsustainable".
What's a marriage KPI?
Ma also raised eyebrows at a company wedding this year when he declared the key to a balanced personal life came down to the bizarre "669" rule.
"At work, we emphasise the spirit of 996. In life, we should follow 669," Ma told couples gathered before him, according to the ABC.
"We want 669 in life. What is 669? Six times in six days, the emphasis is on nine."
He also encouraged them to "work happily and live seriously" and said the "KPI" of marriage was to procreate.
"The first KPI of marriage is to have results. There must be products. What is the product? Have children," Ma said.
"Marriage is not for the purpose of accumulating wealth, not for buying a house, not for buying a car, but for having a child together."
What now for the multinational conglomerate?
The departure of charismatic founders from big tech companies typically causes hand-wringing and wobbling share prices but not at Alibaba.
The company's operational reins have for a couple of years now been in the hands of a respected team of executives who have kept it on e-commerce's cutting edge.
Ma was Alibaba's driving force and a frequently irreverent ambassador for the company, known for stunts like a Michael Jackson-inspired dance at an Alibaba anniversary celebration two years ago and starring in his own kung fu short film.
Gold standard
He is expected to retain some advisory functions.
But the transition to figures like CEO Daniel Zhang and co-founder and executive vice-chairman Joseph Tsai — announced a year ago — may prove to be the "gold standard" for tech-company succession, said Jeffrey Towson, an equity investor and professor at Peking University.
"He's succeeded at what Steve Jobs, Bill Gates and (Yahoo co-founder) Jerry Yang failed at, which is making themselves redundant," said Prof Towson, who has authored books on China's leading companies.
"He built a really robust culture at Alibaba and they are still just innovating like crazy."
Ma was a cash-strapped Chinese entrepreneur when he convinced friends to give him nearly A$90,000 to start Alibaba in the eastern city of Hangzhou in 1999.
With monthly active users of more than 750 million today, Alibaba helped to unlock China's massive consumer power, coincidentally a key objective of the Government today as its seeks to fuel domestic demand to lessen the reliance on fickle foreign trade.
Its Taobao and Tmall platforms have helped countless businesses grow.
"(Ma) has been the driving force for the development of China's internet industry and economy. He is (China's) entrepreneurial godfather," said furniture maker Cheng Huaibao.
Cheng, 30, is one of millions of small businessmen often located in so-called "Taobao villages" — communities whose economies are oriented towards Alibaba's vast market — who leapt into commerce thanks to the company.
Cheng started making bunk beds in 2010 in eastern Jiangsu province with 10 staff. Today his thriving operation has 100 employees.
"Without Teacher Ma, I wouldn't have come out and started my own business," Cheng said, using a common Chinese term of respect.
